Reaktionsgleichung
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li][CH2:15]CCC.CCCCCC.C([O:27][C:28](=O)[C:29]([F:32])([F:31])[F:30])C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([C:28]([OH:27])([CH3:15])[C:29]([F:32])([F:31])[F:30])[N:10]([CH3:13])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (1.5 g, 8.6 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (4.1 mL, 10.3 mmol) is added and stirred for 1.5 hours followed by the addition of trifluoro-acetic acid ethyl ester (1.5 g, 10.3 mmol). After 10 min the ice bath is removed and the reaction is allowed to reach room temperature. Then the reaction is cooled down to −78° C. again and methylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added. After 5 min the ice bath is removed and the mixture is stirred at room temperature for 3 hour, poured into water, separated, and the water layer is extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 288.1 (M+1).
Aufarbeitung
- customAfter 10 min the ice bath is removed
- customto reach room temperature
- additionmethylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added
- customAfter 5 min the ice bath is removed
- stirringthe mixture is stirred at room temperature for 3 hour
- additionpoured into water
- customseparated
- extractionthe water layer is extracted with DCM
- concentrationconcentrated
- customThe residue is purified by FCC
Quellen und Nachweise
- ORD-Eintrag
- ord-481c7e95d52345e5a01614e6bb39f2fd
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08541432B2
Verknüpfte Notizen
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